References and Notes
1
Thomson RH.
Naturally Occurring Quinones
2nd ed.:
Academic Press;
London:
1971.
p.282 ; see also p. 597
2
Wang W.
Li T.
Milburn R.
Yates J.
Hinnant E.
Luzzio MJ.
Noble SA.
Attardo G.
Bioorg. Med. Chem. Lett.
1998,
8:
1579
3a
Hayashi T.
Smith FT.
Lee KH.
J. Med. Chem.
1987,
30:
2005
3b
Lee H.
Hong SH.
Kim YH.
Bioorg. Med. Chem. Lett.
1996,
8:
933
4
Brimble MA.
Nairn MR.
Prabaharan H.
Tetrahedron
2000,
56:
1937
5
Naruta Y.
Maruyama J.
Recent Advances in the Synthesis of Quinonoid Compounds. The Chemistry of Quinonoid Compounds
Vol. 2:
Patai S.
Rapoport Z.
John Wiley;
New York:
1988.
p.241
6 Van Puyvelde, L.; Hakizayezu, D.; Brioen, P.; De Kimpe, N.; De Vroey, C.; Bogaerts, J.; Hakizamungu, E., presented at International Congress on Natural Products Research, July 31 to August 4, 1994; Halifax, Canada, 1994.
7a
Hari L.
De Buyck L.
De Pooter HL.
Phytochemistry
1991,
30:
1726
7b
De Kimpe N.
Van Puyvelde L.
Schripsema J.
Erkelens C.
Verpoorte R.
Magn. Reson. Chem.
1993,
31:
329
8
Kesteleyn B.
Van Puyvelde L.
De Kimpe N.
J. Org. Chem.
1999,
64:
438
9
Nguyen Van T.
De Kimpe N.
Tetrahedron Lett.
2004,
45:
3443
10
Kesteleyn B.
De Kimpe N.
Van Puyvelde L.
J. Org. Chem.
1999,
64:
1173
11
Nguyen Van T.
Kesteleyn B.
De Kimpe N.
Tetrahedron
2001,
57:
4213
12
Nguyen Van T.
De Kimpe N.
Tetrahedron
2003,
59:
5941
13 De Kimpe, N.; Kesteleyn, B.; Nguyen, Van T.; Van Puyvelde, L. 18th International Congress of Heterocyclic Chemistry, July 29 to August 3, 2001; Yokohama, Japan, 2001, 120.
14
Pialat J.-P.
Hoffmann P.
Moulis C.
Fouraste I.
Labidalle S.
Nat. Prod. Lett.
1998,
12:
23
15
Kesteleyn B.
De Kimpe N.
Van Puyvelde L.
Synthesis
1999,
1881
16
Bulbule VJ.
Koranne PS.
Munot YS.
Borate HB.
Deshpande VH.
Synth. Commun.
2003,
33:
587
17
Kobayashi K.
Uchida M.
Uneda T.
Tanmatsu M.
Morikawa O.
Konishi H.
Tetrahedron Lett.
1998,
39:
7725
18
Deshpande PP.
Price KN.
Baker DC.
J. Org. Chem.
1996,
61:
455
19
Cossy J.
Taillier C.
Bellosta V.
Tetrahedron Lett.
2002,
43:
7263
20
Eiden F.
Wanner KT.
Arch. Pharm.
1985,
548
21a
Kraus GA.
Sugimoti H.
Tetrahedron Lett.
1978,
2263
21b
Kraus GA.
Cho H.
Crowley S.
Roth B.
Sugimoto H.
Prugh S.
J. Org. Chem.
1983,
48:
3499
22a
Hauser FM.
Mal D.
J. Am. Chem. Soc.
1983,
105:
5688
22b
Hauser FM.
Rhee RP.
J. Org. Chem.
1978,
43:
178
22c
Hauser FM.
Rhee RP.
J. Am. Chem. Soc.
1979,
101:
1628
23
Mitchell AS.
Russell RA.
Tetrahedron
1995,
51:
5207
24a
Gould SJ.
Melville CR.
Tetrahedron Lett.
1997,
38:
1473
24b
Cone MC.
Melville CR.
Gore MP.
Gould SJ.
J. Org. Chem.
1993,
58:
1058
24c
Pedersen JA.
Spectrochim. Acta, Part A
2002,
52:
1257
25
5,10-Dimethoxy-1
H
-benzo[
g
]isochromene-4-one (
13): yellowish oil; 1H NMR (acetone-d
6): δ = 3.90 (3 H, s, OCH3), 4.01 (3 H, s, OCH3), 4.30 (2 H, s, CH2C=O), 5.06 (2 H, s, CH2O), 7.62 (1 H, ddd, J = 8.4, 7.0, 1.4 Hz, CH-7), 7.73 (1 H, ddd, J = 8.4, 7.0, 1.4 Hz, CH-8), 8.11 (1 H, dd, J = 8.4, 1.4 Hz, CH-9), 8.34 (1 H, dd, J = 8.4, 1.4 Hz, CH-6). 13C NMR (acetone-d
6): δ = 62.13 (OCH3), 63.14 (OCH3), 64.46 (CH2O), 74.50 (CH2OC=O), 118.30 (Cquat), 122.01 (CH-9), 125.05 (CH-6), 126.84 (CH-7), 127.45 (Cquat), 129.08 (Cquat), 129.74 (CH-8), 131.74 (Cquat), 146.43 (Cquat), 155.64 (Cquat), 193.47 (C=O). IR (KBr): νmax 1689 (C=O) cm-1. MS (ES+): m/z = 258 [M+].
26
Giles RGF.
Green IR.
Taylor CP.
Tetrahedron Lett.
1999,
40:
4871
27
4-Hydroxy-3,4-dihydro-1
H
-benzo[
g
]isochromene-5,10-dione (
6): 1H NMR (CDCl3): δ = 3.86 (1 H, dd, J = 12.2, 3.8 Hz, CHCH
a
Hb), 4.03 (1 H, dd, J = 12.2, 3.5 Hz, CHCHa
H
b
), 4.49 (1 H, dd, J = 18.9, 1.65 Hz, OCH
a
Hb), 4.76 (1 H, dd, J = 18.9, 0.6 Hz, OCHa
H
b
), 4.82 (1 H, m, CHOH), 7.76 (2 H, m, CH7-CH8), 8.09 (2 H, m, CH6-CH9). 13C NMR (CDCl3): δ = 60.18 (CH2O), 63.23 (CHOH), 69.51 (CH2), 126.38 (C-6 or C-9), 126.63 (C-9 or C-6), 131.83 (2 × Cquat), 134.28 (C-7 and C-8), 140.58 (Cquat), 143.74 (Cquat), 183.84 (C=O), 184.59 (C=O). IR (KBr): νmax = 3468 (OH), 1661 (C=O) cm-1. MS (ES+): m/z (%) = 231 (15) [M + H+], 213 (100) [M+ - H2O].
